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Version: 17.06d (Release date: 2017-06-26)
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Lapachone (Code C28694)

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Terms & Properties

Preferred Name: Lapachone

Definition: A poorly soluble, ortho-naphthoquinone with potential antineoplastic and radiosensitizing activity. Beta-lapachone (b-lap) is bioactivated by NAD(P)H:quinone oxidoreductase-1 (NQO1), creating a futile oxidoreduction that generates high levels of superoxide. In turn, the highly reactive oxygen species (ROS) interact with DNA, thereby causing single-strand DNA breaks and calcium release from endoplasmic reticulum (ER) stores. Eventually, the extensive DNA damage causes hyperactivation of poly(ADP-ribose) polymerase-1 (PARP-1), an enzyme facilitating DNA repair, accompanied by rapid depletion of NAD+/ATP nucleotide levels. As a result, a caspase-independent and ER-stress induced mu-calpain-mediated cell death occurs in NQO1-overexpressing tumor cells. NQO1, a flavoprotein and two-electron oxidoreductase, is overexpressed in a variety of tumors.

Label: Lapachone

NCI Thesaurus Code: C28694 (Search for linked caDSR metadata)  (search value sets)

NCI Metathesaurus Link: C0053471  (see NCI Metathesaurus info)

Synonyms & Abbreviations: (see Synonym Details)
3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione
ARQ501
ARQ 501
Beta-Lap-WJ
Beta-Lapachone
beta-Lapachone
Lapachone
LAPACHONE

External Source Codes: 
CAS Registry Number 4707-32-8 (see NLM ChemIDplus info)
FDA UNII Code 6N4FA2QQ6A
NSC Code 26326 (see NCI DTP info)
NSC Code 629749 (see NCI DTP info)
PDQ Closed Trial Search ID 357565
PDQ Open Trial Search ID 357565 (check for NCI PDQ open clinical trial info)
UMLS CUI C0053471

Other Properties:
     Name Value (qualifiers indented underneath)
Chemical_Formula C15H14O3
code C28694
Contributing_Source FDA
Legacy_Concept_Name beta-Lapachone
Semantic_Type Organic Chemical
Semantic_Type Pharmacologic Substance

Additional Concept Data: 
Defined Fully by Roles: No  

URL: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&code=C28694

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